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Synthesis of Cyclic Dipeptides by Ring‐Closing Metathesis
Author(s) -
Reichwein John F.,
Liskamp Rob M. J.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200006)2000:12<2335::aid-ejoc2335>3.0.co;2-c
Subject(s) - chemistry , ring closing metathesis , amide , substituent , lithium amide , metathesis , ruthenium , ring (chemistry) , grubbs' catalyst , lithium (medication) , combinatorial chemistry , cyclic peptide , organic chemistry , catalysis , stereochemistry , enantioselective synthesis , peptide , polymerization , biochemistry , polymer , medicine , endocrinology
Several cyclic dipeptides ( 4a − g and 9a − c ) have been synthesized by “amide‐to‐amide” cyclization of 2a − g and 8a − c , respectively, by means of ring‐closing metathesis employing the Grubbs ruthenium catalyst. The influence of additives as well as the length of the amide substituent were studied. Best yields were obtained by cyclization in solution with either lithium fluoroacetate or α,α‐dichlorotoluene as an additive.